Sodium Carbonate → HCID 22678749, compound

HRID 1837771Notes

Reaction equation

HRID 1837771 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:13][CH2:12]2)[C:5]([O:8]C)=[N:6][CH:7]=1.S(Cl)(Cl)=[O:31].[C:34](=[O:37])([O-:36])[O-].[Na+].[Na+]>C(O)C>[C:26]([OH:25])(=[O:31])[C:34]([OH:36])=[O:37].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:15][CH2:16]2)[C:5](=[O:8])[NH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 22678358HCID 22678358, compound

Product 1

HCID 22678749HCID 22678749, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (10 ml) was dissolved 443 mg of 1-[(5-chloro-2-methoxy-3-pyridinyl)methyl]-4-[2-[2-(isobutyloxy)phenyl]ethyl]piperidine. To the mixture was added 0.5 ml of thionyl chloride, followed by heating under reflux for 3 hours. An aqueous sodium carbonate was added to the reaction solution, and the mixture was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The resulting oil was dissolved in ethanol, 99 mg of oxalic acid was added thereto, and then the resulting precipitates were collected by filtration, to give 382 mg of the title compound as a white powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. dissolutionThe resulting oil was dissolved in ethanol
  7. addition99 mg of oxalic acid was added
  8. customthe resulting precipitates
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-286e4c4498eb4eb59603a479288dcc99
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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